What are the cheapest airlines to fly from Chicago to Jamaica one-way?

One-way options have recently been found by users for as low as $107 on Spirit Airlines. Other airlines that offer cheap prices include Frontier from $192 and American Airlines from $196 one-way.

What are the most popular routes from Chicago to Jamaica?

The most popular flight routes from Chicago to Jamaica are Chicago O'Hare Intl - Montego Bay Sangster Intl, Chicago Midway - Montego Bay Sangster Intl and Chicago O'Hare Intl - Kingston Norman Manley.

What are the cheapest flights from Chicago to Jamaica?

On average you can expect to pay $702 for a flight from Chicago to Jamaica. The cheapest flight overall is $252 while the most popular route, (Chicago O'Hare Intl - Montego Bay Sangster Intl) is currently priced at $294.

What are the most popular airlines that fly from Chicago to Jamaica?

American Airlines, Delta and Spirit Airlines are the most popular airlines when flying from Chicago to Jamaica.

What is the cheapest day to fly round-trip from Chicago to Jamaica?

Users have found that flying from Chicago to Jamaica on a Wednesday typically leans towards higher prices. However, this doesn’t mean you still can’t find a deal. Flexibility with other aspects of your flight can still land a great price for your trip.

How far in advance should I book a flight from Chicago to Jamaica?

Find a great deal and save up to 49% by booking at least 56 days prior to your desired departure date, rather than waiting until the week of travel. According to our data, there are a number of flights available from Chicago to Jamaica within the next two weeks, with the cheapest ticket starting at $515.

What is the cheapest month to fly from Chicago to Jamaica?

Our data shows that February tends to be the cheapest month to fly to Jamaica from Chicago. Users have commonly found prices around $574 for the month, but tickets can be as low as $344. Due to multiple factors, prepare for potentially higher prices in March.

Can I find deals for flights from Chicago to Jamaica that include hotel bookings?

Yes. In addition to deals on Chicago to Jamaica flights, Cheapflights offers vacation packages that include both flights and hotel.

How can I find direct flights from Chicago to Jamaica?

After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Jamaica.

Can I find deals for business class flights from Chicago to Jamaica?

Yes. Cheapflights offers flight deals from Chicago to Jamaica by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

$447+ Flights from Chicago to Jamaica - Compare & Save Big

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Cheap flight deals from Chicago to Jamaica

Most accurate provider	AranGrant 3 stars
Most trusted provider	AranGrant 3 stars
Round-trip from	$328 (Cheapflightsfares)
One-way from	$107 (Priceline)
Popular in	March
Cheapest in	February
Average price	$549
Good round-trip deal	$543 or less
Good one-way deal	$252 or less

Provider with most accurate pricing for Chicago (CHI)-Montego Bay Sangster Intl flight deals.

Search Deals

Provider most trusted by Cheapflights users for Chicago (CHI)-Montego Bay Sangster Intl flights.

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From Chicago (CHI) to Jamaica

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One-way flight from Chicago (CHI) to Jamaica

Search Deals

Highest demand for flights based on searches. 1% potential increase in price ($6 potential increase over avg. RT price).

Search Deals

Cheapest flight prices on average. 1% potential price decrease ($10 potential savings vs. average RT price).

Search Deals

Average for round-trip flights in May 2025

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Price to beat on a round-trip flight from Chicago (CHI) to Jamaica.

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Price to beat on a one-way flight from Chicago (CHI) to Jamaica.

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Find flight deals from Chicago to Jamaica

Cheapest flights from Chicago to Jamaica
Explore the most affordable flight options available from Chicago to Jamaica. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 1, 2025.

Wed 5/285:05 amORD - KIN

1 stop7h 24mSpirit Airlines

Wed 6/41:34 pmKIN - ORD

1 stop9h 30mSpirit Airlines

Deal found 4/30

$311

Wed 10/155:05 amORD - MBJ

1 stop6h 36mSpirit Airlines

Mon 10/2012:46 pmMBJ - ORD

1 stop7h 54mSpirit Airlines

Deal found 4/30

$445

Mon 8/258:30 amORD - MBJ

Nonstop4h 01mAmerican Airlines

Fri 8/292:00 pmMBJ - ORD

Nonstop4h 30mAmerican Airlines

Deal found 4/30

$446

Tue 5/274:46 pmMDW - MBJ

1 stop15h 04mFrontier

Sat 5/318:55 amMBJ - MDW

1 stop13h 22mFrontier

Deal found 4/30

$447

Wed 5/76:00 amMDW - MBJ

1 stop9h 30mDelta

Wed 5/141:02 pmMBJ - MDW

1 stop8h 26mDelta

Deal found 4/30

$449

Thu 5/226:26 pmORD - MBJ

1 stop13h 24mMultiple Airlines

Wed 5/2812:07 pmMBJ - ORD

1 stop10h 57mMultiple Airlines

Deal found 4/30

$449

Fri 6/1312:44 pmMDW - KIN

1 stop7h 16mDelta

Fri 6/209:00 amKIN - MDW

1 stop9h 02mDelta

Deal found 4/30

$451

Wed 6/187:01 amORD - KIN

2 stops12h 54mAmerican Airlines

Sat 7/126:00 amKIN - ORD

1 stop16h 44mAmerican Airlines

Deal found 4/30

$456

Fri 5/95:31 pmORD - MBJ

1 stop20h 22mFrontier

Mon 5/122:08 pmMBJ - ORD

1 stop9h 03mFrontier

Deal found 4/30

$458

Sat 6/1411:20 amORD - KIN

1 stop8h 40mDelta

Sat 6/219:00 amKIN - ORD

1 stop8h 11mDelta

Deal found 4/30

$461

Sun 6/89:00 amMDW - MBJ

Nonstop4h 00mSouthwest

Tue 6/102:20 pmMBJ - MDW

Nonstop4h 10mSouthwest

Deal found 4/30

$462

Tue 5/65:55 amORD - KIN

2 stops30h 34mMultiple Airlines

Wed 5/147:05 amKIN - ORD

2 stops15h 34mMultiple Airlines

Deal found 4/30

$478

Best flights from Chicago to Jamaica
Discover carefully curated flight deals from Chicago to Jamaica that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 1, 2025.

Fri 5/235:05 amORD - KIN

1 stop7h 24mSpirit Airlines

Fri 5/301:34 pmKIN - ORD

1 stop10h 31mSpirit Airlines

Deal found 4/29

$328

Tue 6/108:05 amORD - KIN

2 stops11h 50mAmerican Airlines

Wed 7/26:00 amKIN - ORD

1 stop13h 45mAmerican Airlines

Deal found 4/28

$446

Tue 5/274:46 pmMDW - MBJ

1 stop15h 04mFrontier

Sat 5/318:55 amMBJ - MDW

1 stop13h 22mFrontier

Deal found 4/30

$447

Mon 5/56:20 amORD - MBJ

1 stop6h 22mMultiple Airlines

Fri 5/912:07 pmMBJ - ORD

1 stop11h 58mMultiple Airlines

Deal found 4/30

$448

Wed 5/76:00 amMDW - MBJ

1 stop9h 30mDelta

Wed 5/141:02 pmMBJ - MDW

1 stop8h 26mDelta

Deal found 4/30

$449

Sun 6/89:00 amMDW - MBJ

Nonstop4h 00mSouthwest

Tue 6/102:20 pmMBJ - MDW

Nonstop4h 10mSouthwest

Deal found 4/30

$462

Fri 7/181:07 amORD - MBJ

1 stop10h 08mCopa Airlines

Fri 7/2512:14 pmMBJ - ORD

1 stop12h 06mCopa Airlines

Deal found 4/29

$468

Sun 7/138:42 amORD - MBJ

Nonstop4h 07mUnited Airlines

Sun 7/201:51 pmMBJ - ORD

Nonstop4h 29mUnited Airlines

Deal found 4/29

$501

Sun 7/139:14 pmORD - MBJ

1 stop14h 01mAir Canada

Mon 7/2112:10 pmMBJ - ORD

1 stop20h 59mAir Canada

Deal found 4/30

$531

Thu 10/91:35 pmORD - KIN

1 stop10h 14mJetBlue

Tue 10/149:05 amKIN - ORD

1 stop11h 49mJetBlue

Deal found 4/29

$563

Wed 5/75:05 amORD - MBJ

1 stop5h 57mSpirit Airlines

Sun 5/1112:07 pmMBJ - ORD

2 stops11h 22mSpirit Airlines

Deal found 4/30

$447

Tue 5/279:00 amORD - MBJ

Nonstop4h 00mAmerican Airlines

Tue 6/312:54 pmMBJ - ORD

1 stop11h 02mAmerican Airlines

Deal found 4/29

$451

Last-minute flights from Chicago to Jamaica
Discover last-minute flight deals from Chicago to Jamaica. Data last updated May 1, 2025 and is based on user searches.

Thu 5/15:30 amORD - MBJ

1 stop6h 27mDelta

Tue 5/61:22 pmMBJ - ORD

1 stop10h 37mDelta

Deal found 4/30

$551

Mon 5/56:20 amORD - MBJ

1 stop6h 22mMultiple Airlines

Fri 5/912:07 pmMBJ - ORD

1 stop11h 58mMultiple Airlines

Deal found 4/30

$448

Tue 5/67:47 pmORD - KIN

1 stop16h 42mSpirit Airlines

Wed 5/141:34 pmKIN - ORD

1 stop9h 30mSpirit Airlines

Deal found 4/30

$408

Tue 5/65:55 amORD - KIN

2 stops30h 34mMultiple Airlines

Wed 5/147:05 amKIN - ORD

2 stops15h 34mMultiple Airlines

Deal found 4/30

$478

Wed 5/75:05 amORD - MBJ

1 stop5h 57mSpirit Airlines

Sun 5/1112:07 pmMBJ - ORD

2 stops11h 22mSpirit Airlines

Deal found 4/30

$447

Wed 5/76:00 amMDW - MBJ

1 stop9h 30mDelta

Wed 5/141:02 pmMBJ - MDW

1 stop8h 26mDelta

Deal found 4/30

$449

Wed 5/79:00 amORD - MBJ

Nonstop4h 00mAmerican Airlines

Sun 5/1112:54 pmMBJ - ORD

1 stop11h 02mAmerican Airlines

Deal found 4/30

$470

Thu 5/84:15 pmORD - MBJ

2 stops18h 47mMultiple Airlines

Tue 5/1312:07 pmMBJ - ORD

1 stop20h 43mMultiple Airlines

Deal found 4/30

$460

Thu 5/87:25 pmMDW - MBJ

2 stops47h 01mWestJet

Wed 5/1412:45 pmMBJ - MDW

2 stops29h 00mWestJet

Deal found 4/30

$3,299

Fri 5/95:31 pmORD - MBJ

1 stop20h 22mFrontier

Sun 5/112:07 pmMBJ - ORD

1 stop21h 56mFrontier

Deal found 4/30

$448

Fri 5/91:19 pmMDW - MBJ

2 stops24h 34mFrontier

Sun 5/112:07 pmMBJ - MDW

1 stop9h 47mFrontier

Deal found 4/30

$550

Fri 5/95:31 pmORD - MBJ

1 stop20h 22mFrontier

Mon 5/122:08 pmMBJ - ORD

1 stop9h 03mFrontier

Deal found 4/30

$458

One-way flights from Chicago to Jamaica
Search for one-way flight options from Chicago to Jamaica. Find affordable one-way fares based on user searches. Data last updated May 1, 2025.

Wed 5/75:05 amORD - MBJ

1 stop5h 57mSpirit Airlines

Deal found 4/30

$107

Sat 6/214:45 pmORD - KIN

1 stop19h 43mSpirit Airlines

Deal found 4/30

$150

Mon 7/79:12 pmMDW - MBJ

2 stops13h 50mMultiple Airlines

Deal found 4/30

$165

Wed 5/285:03 pmORD - MBJ

2 stops17h 59mMultiple Airlines

Deal found 4/29

$176

Fri 5/308:55 pmMDW - MBJ

1 stop14h 58mFrontier

Deal found 4/30

$192

Wed 5/79:00 amORD - MBJ

Nonstop4h 00mAmerican Airlines

Deal found 4/30

$196

Tue 5/276:00 amMDW - MBJ

1 stop6h 58mDelta

Deal found 4/29

$201

Sat 6/1410:26 amMDW - KIN

1 stop9h 34mDelta

Deal found 4/30

$202

Sat 6/147:05 amORD - KIN

2 stops12h 55mDelta

Deal found 4/30

$202

Sat 6/146:15 amORD - MBJ

1 stop9h 25mJetBlue

Deal found 4/30

$203

Sun 6/299:00 amMDW - MBJ

Nonstop4h 00mSouthwest

Deal found 4/30

$203

Tue 7/221:07 amORD - MBJ

1 stop10h 08mCopa Airlines

Deal found 4/30

$206

Cheapflights Fare Finder

Use the filters below to find and compare flights from Chicago to Jamaica that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Wed 5/28

5:05 am-12:29 pm

1 stop7h 24m

Kingston Norman Manley

Wed 6/4

1:34 pm-11:04 pm

1 stop9h 30m

$311

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Wed 10/15

5:05 am-11:41 am

1 stop6h 36m

Montego Bay Sangster Intl

Mon 10/20

12:46 pm-8:40 pm

1 stop7h 54m

$445

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Mon 8/25

8:30 am-12:31 pm

Nonstop4h 01m

Montego Bay Sangster Intl

Fri 8/29

2:00 pm-6:30 pm

Nonstop4h 30m

$446

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Tue 5/27

4:46 pm-7:50 am

1 stop15h 04m

Montego Bay Sangster Intl

Sat 5/31

8:55 am-10:17 pm

1 stop13h 22m

$447

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sun 8/10

5:42 pm-11:41 am

2 stops17h 59m

Montego Bay Sangster Intl

Thu 8/14

9:05 am-10:25 am

1 stop25h 20m

$448

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Fri 6/13

12:44 pm-8:00 pm

1 stop7h 16m

Kingston Norman Manley

Fri 6/20

9:00 am-6:02 pm

1 stop9h 02m

$451

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Wed 6/18

7:01 am-7:55 pm

2 stops12h 54m

Kingston Norman Manley

Sat 7/12

6:00 am-10:44 pm

1 stop16h 44m

$456

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Mon 8/25

6:00 am-11:49 am

1 stop5h 49m

Montego Bay Sangster Intl

Fri 8/29

1:15 pm-9:47 pm

1 stop8h 32m

$461

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Sat 6/14

9:40 am-8:00 pm

1 stop10h 20m

Kingston Norman Manley

Sat 6/21

9:00 am-7:30 pm

1 stop10h 30m

$461

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sun 6/8

9:00 am-1:00 pm

Nonstop4h 00m

Montego Bay Sangster Intl

Tue 6/10

2:20 pm-6:30 pm

Nonstop4h 10m

$462

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/30

Showing 1-10 of 41 results

...

Best time to book a flight from Chicago to Jamaica

Have a flexible travel schedule? Discover the best time to fly to Jamaica from Chicago with our price prediction graph.

Estimated round-trip price

Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago to Jamaica

What is the cheapest month to book a flight from Chicago to Jamaica?

Currently, January is the cheapest month in which you can book a flight from Chicago to Jamaica (average of $403). Flying from Chicago to Jamaica in July is currently the most expensive (average of $569). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from CHI to JM?

When flying from Chicago to Jamaica, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

What is the cheapest day to fly from Chicago to Jamaica?

Travelers seeking maximum savings on their Chicago to Jamaica flight should consider departing on Sunday mornings when fares are most often at their lowest. Thursday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Chicago to Jamaica

The most flights from CHI to JM0 are scheduled on a Monday (2 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (1 on average).

Rainfall in Jamaica by month

In terms of precipitation, rainfall in Jamaica ranges from 1.6 - 7.1 inches per month. October is typically the wettest month, when rainfall can reach 7.1 in. February is typically the driest time to visit Jamaica when rainfall is around 1.6 in.

Temperature in Jamaica by month

If weather is an important factor for your trip to Jamaica, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 77.0 F).

Reviews of airlines servicing Jamaica

See what other customers who have flown with Southwest, Delta and Copa Airlines from Chicago to Jamaica have to say. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.

Southwest

8.0

Very good

4,294 reviews

Reviews

1 / 20

10.0

Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!

Southwest

8.0

Very good

4,294 reviews

Southwest

8.0

Very good

4,294 reviews

Reviews

1 / 20

10.0

Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!

Delta

8.0

Very good

7,934 reviews

Southwest

8.0

Very good

4,294 reviews

Reviews

1 / 20

10.0

Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!

Copa Airlines

7.5

Good

1,414 reviews

Southwest

8.0

Very good

4,294 reviews

Reviews

1 / 20

10.0

Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!

United Airlines

7.4

Good

8,696 reviews

Southwest

8.0

Very good

4,294 reviews

Reviews

1 / 20

10.0

Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!

JetBlue

7.3

Good

2,922 reviews

Southwest

8.0

Very good

4,294 reviews

Reviews

1 / 20

10.0

Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!

Related info for your journey

What are the cheapest airlines to fly from Chicago to Jamaica one-way?
One-way options have recently been found by users for as low as $107 on Spirit Airlines. Other airlines that offer cheap prices include Frontier from $192 and American Airlines from $196 one-way.
What are the most popular routes from Chicago to Jamaica?
The most popular flight routes from Chicago to Jamaica are Chicago O'Hare Intl - Montego Bay Sangster Intl, Chicago Midway - Montego Bay Sangster Intl and Chicago O'Hare Intl - Kingston Norman Manley.
What are the cheapest flights from Chicago to Jamaica?
On average you can expect to pay $702 for a flight from Chicago to Jamaica. The cheapest flight overall is $252 while the most popular route, (Chicago O'Hare Intl - Montego Bay Sangster Intl) is currently priced at $294.
Can I find deals for flights from Chicago to Jamaica that include hotel bookings?
Yes. In addition to deals on Chicago to Jamaica flights, Cheapflights offers vacation packages that include both flights and hotel.
How can I find direct flights from Chicago to Jamaica?
After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Jamaica.
Can I find deals for business class flights from Chicago to Jamaica?
Yes. Cheapflights offers flight deals from Chicago to Jamaica by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.
What is the cheapest month to book a flight from Chicago to Jamaica?
Currently, January is the cheapest month in which you can book a flight from Chicago to Jamaica (average of $403). Flying from Chicago to Jamaica in July is currently the most expensive (average of $569). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Alternative routes for Chicago to Jamaica

O'Hare Intl to Luis Munoz Marin Intl flights

O'Hare Intl to Punta Cana flights

Midway to Luis Munoz Marin Intl flights

O'Hare Intl to Montego Bay flights

Midway to Punta Cana flights

O'Hare Intl to Oranjestad flights

O'Hare Intl to Castries flights

Midway to Montego Bay flights

St. Louis to Luis Munoz Marin Intl flights

O'Hare Intl to Saint Thomas Island flights

O'Hare Intl to Nassau flights

O'Hare Intl to Willemstad flights

O'Hare Intl to Providenciales flights

St. Louis to Punta Cana flights

O'Hare Intl to George Town flights

O'Hare Intl to Santo Domingo flights

O'Hare Intl to Christiansted flights

O'Hare Intl to Simpson Bay flights

St. Louis to Montego Bay flights

St. Louis to Saint Thomas Island flights

Midway to Oranjestad flights

O'Hare Intl to Kingston flights

O'Hare Intl to Bridgetown flights

Midway to Saint Thomas Island flights

St. Louis to Nassau flights

O'Hare Intl to Puerto Plata flights

Midway to Nassau flights

O'Hare Intl to Santiago de los Caballeros flights

Midway to Providenciales flights

St. Louis to Oranjestad flights

Midway to Santo Domingo flights

St. Louis to Castries flights

Midway to George Town flights

O'Hare Intl to Road Town flights

O'Hare Intl to St. John's flights

Midway to Santiago de los Caballeros flights

St. Louis to Providenciales flights

O'Hare Intl to Kralendijk flights

O'Hare Intl to Pointe-à-Pitre flights

O'Hare Intl to Ponce flights

St. Louis to Simpson Bay flights

Midway to Kingston flights

O'Hare Intl to Castries flights

St. Louis to Willemstad flights

O'Hare Intl to The Valley flights

O'Hare Intl to Gustavia flights

St. Louis to George Town flights

O'Hare Intl to Havana flights

O'Hare Intl to Port of Spain flights

St. Louis to Christiansted flights

Top 5 airlines flying from Chicago to Jamaica

Airline	Cheapest	Average	Flexibility	On-time
Spirit Airlines	Cheapest$273	Average$441	FlexibilityNo cancel fee	On-time65%
Delta	Cheapest$295	Average$831	FlexibilityNo cancel fee	On-timeN/A
American Airlines	Cheapest$393	Average$694	FlexibilityNo cancel fee	On-time71%
United Airlines	Cheapest$396	Average$620	FlexibilityNo cancel fee	On-time69%
Southwest	Cheapest$579	Average$748	FlexibilityNo cancel fee	On-time63%

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$107+ Cheap flights from Chicago (CHI) to Jamaica

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 5/7. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Chicago to Jamaica with Cheapflights

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Cheap flight deals from Chicago to Jamaica

Keep the following information in mind while searching for Chicago to Jamaica flight deals. Data was last updated May 1, 2025.

Most accurate provider

Most trusted provider

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Good round-trip deal

Good one-way deal

Find flight deals from Chicago to Jamaica

Cheapest flights from Chicago to JamaicaExplore the most affordable flight options available from Chicago to Jamaica. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 1, 2025.

Explore the most affordable flight options available from Chicago to Jamaica. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 1, 2025.

Cheapflights Fare Finder

Use the filters below to find and compare flights from Chicago to Jamaica that are best for you.

Best time to book a flight from Chicago to Jamaica

Have a flexible travel schedule? Discover the best time to fly to Jamaica from Chicago with our price prediction graph.

Cheapflights Insights

Everything you need to know about your flight from Chicago to Jamaica

What is the cheapest month to book a flight from Chicago to Jamaica?

What is the cheapest time of day to fly from CHI to JM?

Find hourly flight availability from Chicago to Jamaica. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated May 1, 2025.

What is the cheapest day to fly from Chicago to Jamaica?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Jamaica. Price data was last updated on December 16, 2024.

Weekly flight availability from Chicago to Jamaica

Explore weekly flight availability from Chicago to Jamaica. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated May 1, 2025.

Rainfall in Jamaica by month

Plan your trip to Jamaica by taking into account the average rainfall totals by month.

Temperature in Jamaica by month

Plan your trip to Jamaica by taking into account the average temperature totals by month.

Reviews of airlines servicing Jamaica

Get insights into the airlines that provide service to Jamaica. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Jamaica. Reviews last updated May 1, 2025.

See what other customers who have flown with Southwest, Delta and Copa Airlines from Chicago to Jamaica have to say. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Jamaica. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

What are the cheapest airlines to fly from Chicago to Jamaica one-way?

What are the most popular routes from Chicago to Jamaica?

What are the cheapest flights from Chicago to Jamaica?

Can I find deals for flights from Chicago to Jamaica that include hotel bookings?

How can I find direct flights from Chicago to Jamaica?

Can I find deals for business class flights from Chicago to Jamaica?

What is the cheapest month to book a flight from Chicago to Jamaica?

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Cheapest flights from Chicago to Jamaica
Explore the most affordable flight options available from Chicago to Jamaica. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 1, 2025.